Azo pigments form a 1-aminoanthraquinone diazo component and a phthalimidacetoacetanilide coupling component

ABSTRACT

WHEREIN R1 is H, Cl in the 3- or 4- position to the azo group and R2 is a phthalimide group in the meta-or para position. The yellow pigments are suitable for coloring surface coatings and plastics and for the production of printing inks. The pigments have excellent light fastness properties, weather fastness properties and fastness to over spraying.   Azo pigments of the formula:

United States Patent Dimroth et al.

[ Mar. 18, 1975 Aktiengesellschaft, Ludwigshafen, Rhein, Germany 22 Filed: Apr. 23, 1973 21 Appl. No.: 353,619

[30] Foreign Application Priority 'Data May 17, 1972 Germany..., 2224010 [52] U.S. Cl. 260/152, 106/23 [51] Int. Cl C0910 29/32 [58] Field of Search 260/152, 193

[56] References Cited UNITED STATES PATENTS 2,820,787 H1958 Randall et al 260/193 FOREIGN PATENTS OR APPLICATIONS 1,214,323 12/1970 United Kingdom .260/152 1,221,182 2/1971 United Kingdom ..260/l52 Azo pigments of the 1.224.739 3/1071 United Kin damll..'..'.1.liTI.i6 i/'1sz Primary I:'.\wnim'r-Henry R. Jiles Assistant liruminw-Robert W. Ramsuer Attorney, Agent. or Firm-lohnston, Keil. Thompson & Shurtleff [57] ABSTRACT formula:

COCH:

wherein R is H, C1 in the 3- or 4- position to the azo group and R is a phthalimide group in the meta-or para position. The yellow pigments are suitable for coloring surface coatings and plastics and for the production of printing inks. The pigments have excellent light fastness properties, weather fastness properties and fastness to over spraying.

2 Claims, N0 Drawings is particularly preferred and pigments of the formula (I) with R hydrogen are preferred because of their bright shades and good fastness properties.

The pigments may be prepared by diazotization and tization components, are l-amino-3-chloroanthraquinone and l-amino-4- chloroanthraquinone. Examples of coupling components are the phthalimidacetoacetanilides of the formula (Ill):

in which R has the above meanings.

The pigments are often not in a physical form equally well suited to all applications as obtained in the manufacturing process. They may be adapted to the particular use by conventional methods, for example by heating a suspension in water or in an organic solvent.

The following Examples illustrate the invention. The parts and percentages given in the following Examples are by weight (III) EXAMPLE I 322 parts of particulate 4- phthalimidoacetoacetanilide is suspended in 5,000 parts of Water. Then the diazonium sulfate prepared from 223 parts of l-aminoanthraquinone is added with vigorous stirring at room temperature and the mixture is adjusted to pH 5 with 400 parts of solid anhydrous sodium acetate. The whole is stirred for about another ten hours at room temperature and then the reaction mixture devoid of diazonium salt is heated for another hour at to C, suction filtered while hot, washed with water and dried. 500 parts of a greenish yellow pigment of formula (II) is obtained. I

To optimize the properties of the pigment obtained -it is stirred for from 3 to 4 hours in 10 times its weight of glacial acetic acid at to 1 10 C, suction filtered while hot, washed with water and dried.

EXAMPLES 2 TO 6 The procedure of Example I is repeated but the amines set out in the Table are used as diazotization components and the acetoacetanilides set out therein are used as coupling components. Pigments are obcoupling by conventional methods. Examples of diazo- 45 tained with the hues indicated.

l-aminoanthraquinone,'

TABLE-Continued Amiuonnthrn- Ex. quinonu At'ti0n00ifllllilti0 lliw EXAMPLE 7 parts of the pigment obtained according to Example l and 95 parts of baking varnish mixture [consisting of 70% of coconut alkyd resin (60% in xylene) and of melamine resin (about 55% in a mixture of butanol and xylene)] are ground in an attritor mill. The mixture is applied to a substrate and baked for 30 minutes at 120 C. Brilliant greenish yellow full tone coatings are obtained having very good fastness to light, weathering and overspraying. Reduction with titanium dioxide gives bright shades.

Similar coatings in the hue given in the Table are obtained when the pigments described in the other Exam- I ples are used.

EXAMPLE 8 0.5 part of the pigment obtained according to Example l is incorporated into 100 parts of styrene at from 190 to 200 C in an extruder. A greenish yellow transparent coloration of excellent fastness to light is obtained.

Colorations of good hiding power are obtained by additionally incorporating l part of titanium dioxide.

Similar results are obtained when pigments from Examples 2 to 6 are used.

EXAMPLE 9 8 parts of the pigment obtained according to Example l, parts of rosin modified with phenolformaldehyde and 60 parts of toluene are intimately mixed in a dispersing unit. A greenish yellow toluene intaglio printing ink is obtained having outstanding fastness to light and weathering and outstanding brilto V A Do.

C0 cum 0 or-nc ONH N\ liance.

Similar results are obtained when pigments from Examples 2 to 6 are used.

We claim:

1. An azo pigment of the formula:

in which R is hydrogen or chloro in the meta-position or paraposition to the diazo group; and R is phthalimido in the meta-position or paraposition. 2. The azo pigment of the formula: 

1. AN AZO PIGMENT OF THE FORMULA:
 2. The azo pigment of the formula: 